Acid pyronine dyestuffs



Patented Apr. 23, 1940 ACID PYRONINE DYESTUFFS Paul Herbert Wolfl, deceased, late of Frankfort-1 on-the-Main-Hochst, Germany, by Richard Wenzel, administrator, Frankfort on the- Main-Hochst, Germany, and

Karl 7 Frank,

Frankfort-on-the-Main-Hochst, Germany, assignors to General Aniline & Film Corporation, a corporation of Delaware No Drawing. Application September 29, 1938, Serial No. 232,303. In Germany November 4,

3 Claims.

The present invention relates to acid pyronine dyestuffs. I 7 We have found that acid pyronine dyestuffs are obtainable by condensing a 3.6-di- 5 halogen-xanthone with an isocyclic or heterocyclic secondary or tertiary amine, then exchanging the halogen atoms in 3- and 6-positions for the radicals of an aromatic amine and sulfonating the dyestuffs thus obtained. There 10 are obtained new acid dyestuffs, for instance,

those of the following general formula I SOlNa or the methyl group and R a member of the group consisting of indole radicals and N-alkyl substituted aniline radicals. The new dyestuffs dye animal fibers violet tints of good properties of fastness.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto, the parts being by weight:

1. 13.3 parts of 3.6-dich1oroxanthone, 1 0.0

parts of n-butylethyl-meta-toluidine, 10 parts of phosphorus oxychloride and 8 parts of zinc chloride are together boiled with '75 parts of toluene in a reflux apparatus until hydrochloric acid is.

no longer evolved. The condensation product which has separated is freed from the toluene wherein X represents an alkyl group, Y hydrogen tints of good properties of fastness. It has probably the following constitution:

OH (Hit 0 803B some 10 cnznob-NH- 0/ NH- -0:H5

The 3.6-dichl0roxanthone of the formula: 16

may be prepared as follows:

191 parts of 2.4-dichlorobenzoic acid, 130 parts of metachlorophenol and 120 parts of caustic potash are together heated, while stirring, at 25 195 C. in the presence of parts of methanol, during which operation the methanol, serving as melting agent, distils. After further heating for hour at 195 0. water is added, the mass is acidified and unchanged meta-chlorophenol re- 0 moved by means of steam. The 5.5-dichlorodiphenyl ether-2-carboxy1ic acid at first obtained is heated in ten times its weight of concentrated sulfuric acid for 1 hour at about C. Thereby ring-closure to form the 3.6-dichloroxantho1'1e 35 occurs; this product is separated by pouring the mass on ice and may be purified by recrystallization from alcohol or methanol.

ing as indicated in Example 1, a violet dyestufi of similar properties is obtained.

4. By condensing 13.3 parts of 3.6-dichloroxanthone with 16 parts of l-isobutyl-Z-parachlorophenyl-4.Ei-dimethylindol in the presence of zinc chloride and phosphorus oxv-chloride in toluene, in a manner analogous to that indicated in Example 1, a product is obtained which when melted with parts of N-methyl-para-anisidine at C. and subsequently sulfonated (as described in Example 1) yields a dyestuff which, in the form of the sodium salt, dyes Wool and silk violet tints of good properties of fastness. The dyestufi has probably the following! constitution:

We claim: l 1. The compounds of the general formula:

S 02H S OsNa wherein X represents an alkyl group, Y a member of the group consisting of hydrogen and methyl and. R an indole radical, being acid dyestufis yielding on animal fibers violet tints of good fastness properties.

2. The compound of the formula:

being a dyestufi which dyes wool and silk pure SOsNa 'violet tints of good fastness properties.

3. The compound of the formula:

I RICHARD WENZEL, Administrator of Paul Herbert'WoZfi, Deceased.

KARL FRANKQ. 

